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Festivals, Fairs & Special Events, Music & Comedy, Theatre & Performing Arts
Comic Court: Chicago’s #1 Comedy Court Show
Order in the court!Comic Court is back at The Lincoln Lodge every 2nd & 4th Tuesday at 9PM. Comedians argue ridiculous cases like actual lawyers,…
Tuesday, May 26th
9:00 p.m. – 10:30 p.m.The Lincoln Lodge
2040 North Milwaukee AvenueMuseums, Galleries & Exhibitions
By A Thread: Nature’s Resilience
By A Thread: Nature’s Resilience dives into the science of biodiversity and what it takes to protect it—showcasing the research, conservation, and education work happening…
Wednesday, May 27th
10:00 a.m. – 4:00 p.m.Peggy Notebaert Nature Museum
2430 N. Cannon Dr.Museums, Galleries & Exhibitions
Illinois Holocaust Museum presents Experience360
Illinois Holocaust Museum presents Experience360 provides a panoramic view through history and truth, inviting visitors of all backgrounds to witness stories of survival, ask questions, and reflect…
Wednesday, May 27th
10:00 a.m. – 5:00 p.m.Illinois Holocaust Museum presents Experience360
360 N State StTheatre & Performing Arts
Windfall
This is a story about money. Don’t let them fool you otherwise. When a father loses his child in a clash with the local police,…
Wednesday, May 27th
7:30 p.m. – 9:30 p.m.Steppenwolf Theatre Company
1650 N. Halsted St. , Chicago, IL, 60614Music & Comedy
A$AP Rocky – Don’t Be Dumb World Tour 2026
Hip-hop artist A$AP Rocky is scheduled to kick off his 42-date “Don’t Be Dumb World Tour” in Chicago on Wednesday, May 27, 2026. This tour…
Wednesday, May 27th
7:30 p.m. – 10:30 p.m.United Center
1901 W Madison St,Music & Comedy, Theatre & Performing Arts
Hooch & Holler Comedy Show
Every Wednesday The Best Speakeasy In Chicago Hosts The Hottest Comedians The City Has To Offer! Indulge In Our Amazing Craft Cocktails And Enjoy An…
Wednesday, May 27th
9:00 p.m. – 11:00 p.m.Bordel Cocktail & Cabaret
1721 W DivisionMuseums, Galleries & Exhibitions
By A Thread: Nature’s Resilience
By A Thread: Nature’s Resilience dives into the science of biodiversity and what it takes to protect it—showcasing the research, conservation, and education work happening…
Thursday, May 28th
10:00 a.m. – 4:00 p.m.Peggy Notebaert Nature Museum
2430 N. Cannon Dr.Museums, Galleries & Exhibitions
Illinois Holocaust Museum presents Experience360
Illinois Holocaust Museum presents Experience360 provides a panoramic view through history and truth, inviting visitors of all backgrounds to witness stories of survival, ask questions, and reflect…
Thursday, May 28th
10:00 a.m. – 5:00 p.m.Illinois Holocaust Museum presents Experience360
360 N State StMuseums, Galleries & Exhibitions
American Prophets: Writers, Religion, and Culture
American Prophets journeys through the pages of American history to explore the influence of religion and spirituality on writers and culture, with interactive displays incorporating…
Thursday, May 28th
10:00 a.m. – 5:00 p.m.American Writers Museum
180 N. Michigan Ave.Theatre & Performing Arts
Spamalot
THE SHOW THAT SET BROADWAY BACK 1,000 YEARS…RETURNS! TOURING ACROSS AMERICA THE TONY AWARD-WINNING BEST MUSICAL COMEDY MONTY PYTHON’S SPAMALOT Peter Marks of The Washington…
Thursday, May 28th
5:00 p.m. – 7:00 p.m.CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602Theatre & Performing Arts
Stars & Garters Presents “Stars & Garters After Dark”
Chicago’s brand new Stars & Garters, 3914 N Clark St, presents Stars & Garters After Dark, every Thursday at 7 p.m. in the Rouge Room.…
Thursday, May 28th
7:00 p.m. – 9:30 p.m.Stars and Garters Club
3914 N Clark StTheatre & Performing Arts
Windfall
This is a story about money. Don’t let them fool you otherwise. When a father loses his child in a clash with the local police,…
Thursday, May 28th
7:30 p.m. – 9:30 p.m.Steppenwolf Theatre Company
1650 N. Halsted St. , Chicago, IL, 60614Theatre & Performing Arts
Comedy Hour at Annoyance Theatre
Each week, Chicago comics bring the freshest, most experimental new material to the Annoyance for the Comedy Hour. The weekly show is an eclectic mix…
Friday, May 29th
12:00 a.m. – Saturday, May 30th
1:00 a.m.Annoyance Theatre & Bar
851 W. Belmont Ave., 2nd Fl.Museums, Galleries & Exhibitions
By A Thread: Nature’s Resilience
By A Thread: Nature’s Resilience dives into the science of biodiversity and what it takes to protect it—showcasing the research, conservation, and education work happening…
Friday, May 29th
10:00 a.m. – 4:00 p.m.Peggy Notebaert Nature Museum
2430 N. Cannon Dr.Museums, Galleries & Exhibitions
Illinois Holocaust Museum presents Experience360
Illinois Holocaust Museum presents Experience360 provides a panoramic view through history and truth, inviting visitors of all backgrounds to witness stories of survival, ask questions, and reflect…
Friday, May 29th
10:00 a.m. – 5:00 p.m.Illinois Holocaust Museum presents Experience360
360 N State StMuseums, Galleries & Exhibitions
American Prophets: Writers, Religion, and Culture
American Prophets journeys through the pages of American history to explore the influence of religion and spirituality on writers and culture, with interactive displays incorporating…
Friday, May 29th
10:00 a.m. – 5:00 p.m.American Writers Museum
180 N. Michigan Ave.Theatre & Performing Arts
Spamalot
THE SHOW THAT SET BROADWAY BACK 1,000 YEARS…RETURNS! TOURING ACROSS AMERICA THE TONY AWARD-WINNING BEST MUSICAL COMEDY MONTY PYTHON’S SPAMALOT Peter Marks of The Washington…
Friday, May 29th
5:00 p.m. – 7:00 p.m.CIBC Theatre
18 W. Monroe St. , Chicago, IL, 60602Music & Comedy, Theatre & Performing Arts
The Infinite Wrench
Don’t miss the longest running late-night show in Chicago! At The Infinite Wrench you’ll see 30 original plays in 60 minutes written and performed by…
Friday, May 29th
7:00 p.m. – 8:00 p.m.The Neo-Futurist Theater
5153 N. Ashland Ave.Theatre & Performing Arts
The Improvised Shakespeare Company®
The Improvised Shakespeare Company® proudly presents its critically-acclaimed, long-running hit show Improvised Shakespeare Chicago, now in its 19th year! Join us for an evening of…
Music & Comedy
Devil’s Daughter
The hottest show in town, Devil’s Daughter, features a cast of seasoned comedians who have performed together in Chicago and around the country for over a decade.…
Theatre & Performing Arts
Windfall
This is a story about money. Don’t let them fool you otherwise. When a father loses his child in a clash with the local police,…
Friday, May 29th
7:30 p.m. – 9:30 p.m.Steppenwolf Theatre Company
1650 N. Halsted St. , Chicago, IL, 60614Music & Comedy
Rilo Kiley Live In Concert
Rilo Kiley is scheduled to perform in Chicago, IL, on Friday, May 29, 2026, as part of their reunion tour.
Friday, May 29th
7:30 p.m. – 10:30 p.m.The Chicago Theatre
175 N. StateMusic & Comedy
Summer Walker – Still Finally Over It Tour 2026
R&B star Summer Walker is scheduled to perform in Chicago on Friday, May 29, 2026, as part of her first major arena run, the “Still…
Friday, May 29th
7:30 p.m. – 10:30 p.m.United Center
1901 W Madison St,Music & Comedy
Devil’s Daughter
The hottest show in town Devil’s Daughter features a cast of seasoned comedians who have performed together in Chicago and around the country for over a decade.…
Friday, May 29th
8:00 p.m. – 9:00 p.m.iO Theater
1501 N. Kingsbury St.

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